The Windmill Inn, on Park Road, Heage, will hold the two-day event to raise money for Derbyshire Children’s Holiday Centre.
Lorraine Froggatt, 38, lost her friend John Redfern, 70, to oesophageal cancer in 2013.
Each year since his death Lorraine has hosted a charity event to raise funds.
She hopes to beat last year’s total of more than £6,000.
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She said: “We are raising money for Derbyshire Children’s Holiday Centre as it was a cause very close to John’s heart and we would like to honour that.”
The annual charity weekend, which will kick off on Saturday, September 26, with regulars and community members setting off from the pub at 8.30am, and cycling to the holiday centre in Skegness.
The mother-of-two said: “We have dubbed the cycle ‘Riding for Redders’ – incorporating John’s nickname.
“He was a pillar of the community and we know he would have loved this.
“We hope as many people as possible can get involved and honour his memory while supporting a good cause. Derbyshire children’s holiday centre is an amazing charity and I am very proud to be a part of fundraising for them.”
On the riders’ departure there will be 100 balloons released to mark the start of the event.
After bidding farewell to the cyclists, the pub will host a family afternoon including a bouncy castle, face painting, competitions and live music.
The fun day on September 27 will include darts and dominos competitions, a buffet and a raffle.
Co-organiser Matt Simms added: “This year we have more riders and they will all be wearing our new team jerseys, which this year is sponsored by Valliant.”
To donate to the charity visit: www.justgiving.com/ridingforredders.